In this article, Missouri Supreme Court Judge Michael A. Wolff, who also is distinguished visiting professor at St. Louis University School of Law, outlines the judicial and legislative victories and failures of civil rights advocates over the last forty years at both the federal and state level. He details the reform efforts through personal anecdotes of many of his own cases that he pursued as a legal services lawyer and has seen as a judge. Judge Wolff’s stories focus on the rights that legal services programs fought for and obtained and the battles that continue to be lost. In particular, he looks at both racial and economic inequality in the education system and the penal system. He explores the results of inadequate state funding such as the absence of affordable educational institutions for its citizens. In looking at the penal system, he examines the increasing criminalization of previously non-criminal conduct and the resulting incarceration and its dramatic effect on minority populations. He also discusses the expanding inequality among the United States population as the rich are given disparate tax breaks. Judge Wolff concludes by advocating for continued support of both public education and public health systems and supportive civic institutions.